ISSN:
0170-2041
Keywords:
O-Glycopeptides
;
Solid-phase synthesis
;
Galactose, 2-azido-2-deoxy-D-
;
Peptides
;
Carbohydrates
;
Azido sugars
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A New Strategy for the Solid-Phase Synthesis of O-Glycopeptides via 2-Azido-glycopeptidesThe building blocks Fmoc-Thr(α-D-GalN3Ac3)-OPfp (8) and Fmoc-Ser(α-D-GalN3Ac3)-OPfp (9) were synthesized. Both building blocks are active esters which can directly be used for the solid-phase synthesis of O-glycopeptides. The obtained glycopeptides carry an 2-azido-2-deoxy-D-galactosyl residue α-linked to Thr or Ser. The conversion of the 2-azido into the 2-acetamido groups was achieved with thioacetic acid on solid support, and subsequently the sugar residues of the polymer bound glycopeptides were deacetylated with hydrazine hydrate in methanol. The subsequent cleavage from the resin with TFA/water gave after RP-HPLC purification directly the desired deprotected O-glycopeptides.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940410
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